Separation of an Industrial Mixture of Decalin or Naphthalene Fluorination Products. Purification of Perfluoro(7-methylbicyclo[4.3.0]nonane) from Close-Boiling Impurities by Heteroazeotropic Distillation

A. V. Polkovnichenko; Полковниченко А. В.; E. V. Lupachev; Лупачев Е. В.; A. V. Kisel’; Кисель А. В.; S. Ya. Kvashnin; Квашнин С. Я.; N. N. Kulov; Кулов Н. Н.

doi:10.31857/S0040357123050172

Separation of an Industrial Mixture of Decalin or Naphthalene Fluorination Products. Purification of Perfluoro(7-methylbicyclo[4.3.0]nonane) from Close-Boiling Impurities by Heteroazeotropic Distillation

Authors: Polkovnichenko A.V.¹, Lupachev E.V.¹, Kisel’ A.V.¹, Kvashnin S.Y.¹, Kulov N.N.¹
Affiliations:
1. Kurnakov Institute of General and Inorganic Chemistry RAS
Issue: Vol 57, No 5 (2023)
Pages: 495-506
Section: Articles
URL: https://journals.rcsi.science/0040-3571/article/view/138537
DOI: https://doi.org/10.31857/S0040357123050172
EDN: https://elibrary.ru/MGWEPC
ID: 138537

Cite item

Full Text

Open Access
Restricted Access

Access granted
Restricted Access

Subscription Access

Abstract
About the authors
References
Supplementary files
Statistics

Abstract

The process of perfluoro(7-methylbicyclo[4.3.0]nonane) (MBCN) purification from an industrial mixture of decalin or naphthalene fluorination products is considered. According to experimental data, distillation separation allows us to concentrate MBCN to a fraction with the target-component content of more than 0.950 wt. fr., after which the process efficiency begins to decrease quickly; upon reaching a concentration of 0.975 wt. fr., separation practically breaks down (the value of the separation coefficient Ksep → 1). The process of purification of MBCN by the method of heteroazeotropic distillation using acetone (Aс) as a separating agent is proposed, the process being realized on a batch semi-industrial distillation column. The method makes it possible to intensify significantly the final stage of purification and to increase the MBCN content from 0.950 to more than 0.998 wt. fr., the mass fraction of the enriched fraction sampling comprises more than 0.85 of the load and the product yield being above 88%. The values of the separation coefficients between the distillate and the bottom product and the coefficients of enrichment for the target and impurity components are given; for the MBСN–Aс binary system, data on the liquid–liquid phase equilibrium and heteroazeotrope characteristics are determined.

Keywords

perfluorocycloalkanes, perfluoro(7-methylbicyclo[4.3.0]nonane), perfluorodecalin, separation of isomers, heteroazeotropic distillation, splitting, liquid–liquid equilibrium

References

Aleshinskii V.V., Novikova M.D., Shabalin D.A. Method of Producing Perfluorocycloalkanes // Patent No. RU 2451006 C1. 20 May 2012. https://patents.google.com/patent/RU2451006C1
Gervits L.L., Snegirov V.F., Makarov K.N., Galakhov M.V., Mukhin V.Yu. Non-Chair Conformation of Cis Isomers of 1,4-Disubstituted Perfluorocyclohexanes // Bull. Acad. Sci. USSR Div. Chem. Sci. 1987. V. 36. P. 2664–2665. https://doi.org/10.1007/BF00957267
Gervits L.L. Perfluorocarbon-Based Blood Substitutes Russian Experience // Fluor. Med. 21st Century. 1994. Paper 22. P. 1–9. https://www.researchgate.net/publication/350153316_Perfluorocarbon-Based_Blood_Substitutes_Russian_Experience
Kambur P.S., Pashkevich D.S., Alekseev Yu.I., Yampolskii Yu.P., Alentev A.Yu. Interaction of Perfluorinated Fluids with Fluorine in Gas-Liquid Reactor // Russ. J. Appl. Chem. 2019. V. 92. № 5. P. 661–666. https://doi.org/10.1134/S1070427219050124
Moshnyag A.V., Khoroshilov A.V., Selivanova D.I., Aksenova D.M. Thermodynamics of Dissolved Nitrogen, Nitrous Oxide, and Ammonia in Perfluorodecalin // Russ. J. Phys. Chem. A. 2017. V. 91. № 11. P. 2117–2120. https://doi.org/10.1134/S0036024417100260
Moshnyaga A.V., Khoroshilov A.V., Semyashkin M.P., Mel’nikov V.V. Density of N2O Solutions in Perfluorodecalin As a Function of Concentration // Russ. J. Phys. Chem. A. 2018. V. 92. № 4. P. 719–723. https://doi.org/10.1134/S0036024418040222
Hassanalizadeh R., Nelson W.M., Naidoo P., Ramjugernath D. Measurement and Modeling of the Solubility of Tetrafluoromethane in Either Perfluoroheptane or Perfluorodecalin // J. Chem. Eng. Data. 2020. V. 65. № 10. P. 4862–4868. https://doi.org/10.1021/acs.jced.0c00461
Deepika D., Pandey S. Density and Dynamic Viscosity of Perfluorodecalin-Added n-Hexane Mixtures: Deciphering the Role of Fluorous Liquids // Liquids. 2023. V. 3. № 1. P. 48–56. https://doi.org/10.3390/liquids3010005
Polkovnichenko A.V., Lupachev E.V., Kisel’ A.V., Kvashnin S.Ya., Kulov N.N. Perfluoro(7-Methylbicyclo[4.3.0]Nonane) and Perfluoro(Butylcyclohexane): Physicochemical, Thermophysical, and Spectral Data // J. Chem. Eng. Data. 2023. V. 68. № 3. P. 499–517. https://doi.org/10.1021/acs.jced.2c00588
Wen-Zheng G., Wen-Juan C., Yu-Qing H., Wei-Yuan H. Study on the Vapour Phase Fluorination of Butyl Benzene with Cobalt Trifluoride // Acta Chimica Sinica. 1987. V. 45. № 7. P. 720–723. http://sioc-journal.cn/Jwk_hxxb/EN/Y1987/V45/I7/720
Hynes A.M., Shenton M.J., Badyal J.P.S. Plasma Polymerization of Trifluoromethyl-Substituted Perfluorocyclohexane Monomers // Macromolecules. 1996. V. 29. № 1. P. 18–21. https://doi.org/10.1021/ma950647h
Wells A.W., Diehl J.R., Bromhal G., Strazisar B.R., Wilson T.H., White C.M. The Use of Tracers to Assess Leakage from the Sequestration of CO2 in a Depleted Oil Reservoir, New Mexico, USA // Applied Geochemistry 2007. V. 22. №. 5. P. 996–1016. https://doi.org/10.1016/j.apgeochem.2007.01.002
Tuffin R., Paari O.L., Baker P., Brown C., Sage I.C. Material Combination // Patent No. EP3334801A1. 20 June 2018. https://patents.google.com/patent/EP3334801A1
Dionisio K.L., Phillips K., Price P.S., Grulke C.M., Williams A., Biryol D., Hong T., Isaacs K.K. The Chemical and Products Database, a Resource for Exposure-Relevant Data on Chemicals in Consumer Products // Scientific Data. 2018. 5. Article number: 180125. https://doi.org/10.1038/sdata.2018.125
Tuffin R., Paari O.L., Baker P., Brown C., Sage I.C. Material Combination // Patent No. EP3334801B1. 27 May 2020. https://patents.google.com/patent/EP3334801B1
Moore R.E., Clark L.C. Jr., Miller M.L. Synthesis and Biological Activity of Perfluoroadamantane and Some Closely Related Compounds // International Congress Series. 1979. 486 (Proc. Int. Symp. Perfluorochem. Blood Substitutes). P. 69–79. https://scifinder-n.cas.org/searchDetail/reference/ 64b11cf93459c50ab262f7cc/referenceDetails
Clark L.C. Jr., Moore R.E. Selecting Perfluorocarbon Compounds for Synthetic Blood // Patent No. US4289499 A. 15 September 1981. https://patents.google.com/patent/US4289499A
Rirando C.K.J., Robaato E.M. Determination of Critical Solution Temperatures of Perfluorocarbons // Patent No. JP55095868 A. 21 July 1980. https://worldwide.espacenet.com/patent/search/family/ 025491089/publication/JPS5595868A?q =JPS5595868A
Moore R.E., Clark L.C. Jr. Synthesis and Physical Properties of Perfluorocompounds Useful as Synthetic Blood Candidates // Oxygen Carrying Colloidal Blood Substitutes. 1982. (Int. Symp. Perfluorochem. Blood Substitutes, 5th). P. 50–60. https://scifinder-n.cas.org/searchDetail/reference/ 64b1334c3459c50ab2644c98/referenceDetails
Chung B.H., Lim, Y.T. Cell Labeling and Imaging Using Multifunctional Perfluorocarbon Nanoemulsion // Patent No. WO2009128610 A2. 22 October 2009. https://patents.google.com/patent/WO2009128610A2
Cacheris W.P., Richard T.J., Grabiak R.C., Lee A.C. Paramagnetic Complexes of N-Alkyl-N-Hydroxylamides of Organic Acids and Emulsions Containing Same for Magnetic Resonance Imaging (MRI) // Patent No. US5614170A. 25 March 1997. https://patents.google.com/patent/US5614170A
Ackerman J.L., Clark L.C. Jr., Thomas S.R. Methods for Detecting and Imaging a Temperature of an Object by Nuclear Magnetic Resonance // Patent No. US4558279A. 10 December 1985. https://patents.google.com/patent/US4558279A
Clark L.C. Jr. NMR Compositions for Indirectly Detecting a Dissolved Gas in an Animal // Patent No. US4775522A. 10 April 1988. https://patents.google.com/patent/US4775522A
Kulov N.N., Polkovnichenko A.V., Lupachev E.V., Rastunova I.L., Magomedbekov E.P. Fractionation of D/H and 18O/16O Water Isotopes in a Packed Distillation Column // Theor. Found. Chem. Eng. 2020. V. 54. P. 389–396. https://doi.org/10.1134/S0040579520030094
Polkovnichenko A.V., Lupachev E.V., Kisel’ A.V., Kvashnin S.Y., Kulov N.N. Perfluoro(7-methylbicyclo[4.3.0]-nonane) Purification from Close-Boiling Impurities by Heteroazeotropic Distillation Method. Eng. Proc. 2023, 37, 72. https://doi.org/10.3390/ECP2023-14621